Dimethylformamide → 6-(4-Formyl-phenylsulfanyl)-nicotinamide

HRID 2197630Notes

Reaction equation

HRID 2197630 reaction equation
[SH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Cl[C:11]1[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=[O:16])=[CH:13][N:12]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([S:1][C:11]2[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=[O:16])=[CH:13][N:12]=2)=[CH:3][CH:4]=1)=[O:7]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 804566-ChloronicotinamideHCID 109205784-Sulfanylbenzaldehyde

Product 1

HCID 597178526-(4-Formyl-phenylsulfanyl)-nicotinamideYield 14.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine 4-mercapto-benzaldehyde (0.45 g, 3.3 mmol), 6-chloro-nicotinamide (0.52 g, 3.3 mmol), potassium carbonate (0.7 g, 5.1 mmol), and dimethylformamide (15 mL) then heat at 70° C. overnight. Cool to room temperature, pour into water, and then extract with dichloromethane (3×75 mL). The combined dichloromethane extracts were dried over sodium chloride/magnesium sulfate, filtered, and concentrated on a rotary evaporator to yield the crude product (1 g). The crude product was purified by flash column chromatography on silica gel eluting with 10% aqueous ammonium hydroxide in ethanol and chloroform to yield 6-(4-formyl-phenylsulfanyl)-nicotinamide (120 mg). 1H NMR (DMSO-D6, 300.00 MHz): 10.08 (s, 1H), 8.91 (dd, 1H, J=2.3, 0.7 Hz), 8.18-8.12 (m, 2H), 8.03-7.98 (m, 2H), 7.83-7.78 (m, 2H), 7.61 (s, 1H), 7.34 (dd, 1H, J=8.4, 0.8 Hz).

Workup

  1. extractionextract with dichloromethane (3×75 mL)
  2. dry with materialThe combined dichloromethane extracts were dried over sodium chloride/magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated on a rotary evaporator
  5. customto yield the crude product (1 g)
  6. customThe crude product was purified by flash column chromatography on silica gel eluting with 10% aqueous ammonium hydroxide in ethanol and chloroform

Sources & evidence

ORD record
ord-a65459ccc09b4060a670177815ddd3ca
Source dataset
uspto-grants-2012_12
Patent number
US08338611B2

Reaction notes

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